Finding the Perfect Fit Pt. 10

Sunday Morning

A text from Jamie Saturday night asked if we could go for breakfast the next morning and I agreed, stuck in the cooler at work fighting a tower of Dr. Pepper that was threatening to fall over any second. Of course it did and I had to mop the mess up, hoping a meteor was heading for whoever had fucked up such a simple job of stacking shit!

I made it through the night and passed out once home, waking up to my alarm in confusion before I remembered our date. I showered, dressing in tight jeans and the gray top he'd tried on during some of our fun and got eyeliner and some lip gloss on. During that, I recalled what I'd bought and figured this morning would be the best time to have this conversation... Assuming I could find a way to approach Jamie about it.

Thinking as quickly as my brain, which felt like pudding, would allow me, I found what might have been a viable idea. Pulling the bag of perversion I'd bought out, I placed the strap on and a butt plug on the floor and took a picture. Checking it, I was able to clearly make out what they were and that would have to do.

That done, I texted him and got my car started, the morning clear but freezing. Donna was crashed out on the couch, the table covered in books and her laptop playing an episode of Supernatural, one from the earlier seasons judging by Sam's hair. I was distracted by that for a few minutes before my phone went off, Jamie letting me know he was ready.

Shaking awake, I got behind the wheel and drove over to his dorm, a bleary eyed and baggy clothed Jamie getting in with a sigh.

"I'm just fuckin' done." Clicking the seat belt, he leaned his head back with eyes closed and sighed. I took one of his hands, an eye with a dark crescent under it opening as I leaned towards him. Planting a kiss on a cheek clear of any course facial hair, his lips twitched before he spoke. "Thanks." A squeeze from his hand, one that I returned.

"Of course." I said that while brushing a stray lock of hair out of his face, seeing how tired Jamie was and the tenderness his green eyes showed as he opened them. Slowly, he moved to kiss me and I met him, lips soft and welcoming, running counter to his current mood.

The sound of Jamie's stomach protesting cut through the moment, reducing me to laughter as he looked down in disbelief. "Are you kidding me? Ugh, fine, I guess foods more important than making out." When I was only giggling instead of being trapped in hysterics, I pointed us towards IHOP as he continued to grumble, abet more good natured.

"So what's gotcha stressed: Work or school?" I asked, hoping to help ease his mind and not just cause of what I wanted to talk about later. Though I still had no idea how to bring up the strap on naturally. If that was even possible.

"Fuckin' life in general. I've got a shit ton of homework and my coworkers, who should be old enough to know better, are fucking useless. Tom said I should just let the place burn down and I'm thinking yeah, that's a great idea!" A song came on the classic rock station that made him stop ranting and sit up straight, looking at the radio with such an exaggerated face of disgust I snorted, biting back another laughing fit.

"And then they play Jungle Love?! In the middle of fuckin' winter! Try Trapped Under Ice or... Or anything but Christmas music!" Spluttering in genuine rage, Jamie snapped the radio off as I tried to get my shit under control while navigating a packed parking lot.

"Are ya gonna burn the radio station down too?" Another sigh, Jamie rubbing his face as I turned the car off.

"I just need a break." The volume and tone of his voice dropped and he sounded desperately tired. Leaning forward, hair spilling down in untamed swirls, he wiped sleep from his eyes and spoke with his face hidden away. "I stretched in English the other day and some guy was looking at me weird the rest of class. I think he noticed." Someone walked by my window, reminding me where we were and why. The heat was already starting to lose it's edge and being stuck in the cold probably wasn't going to help Jamie's mood.

"Let's continue this inside, okay?" He nodded and we braved the cold, finding the place packed with the senior crowd as this seemed to be their time. We got seated by a middle aged lady who looked to be on her last nerve and got our orders in for caffeine as the loud, hollow voices of old men rattled surrounded us.

Even looking at the menu, Jamie was discontent and silent, a far cry from the last time I'd seen him. It was the return of the quiet and withdrawn Jamie, hoping to never be noticed. And it was starting to piss me off, that someone who was inoffensive at worst was dealing with so much shit.

"So what if he knows? The semester's over in a month and you'll probably never see him again." Grumbling behind his menu, Jamie glared at a nearby table that was complaining about football at an absurd volume and shook his head.

"I guess but..." That thought trailed off to a sigh, the menu being put down as he began to fiddle with one of the pull strings from his hoodie. Thankfully our caffeine was delivered and that was a temporary bright spot as I sucked down the toxic green Dew.

"Seriously, fuck 'em. This ain't high school, no one gives a shit." True enough, there were too many people here to keep track of.

"I think Tom would disagree." I rolled my eyes and a ghost of a smile touched Jamie's lips, brushing his curling, messy hair away from his face. "I've had to tell him several times I don't care about his basketball drama and he always freaks out, saying it's not drama and then bitching about who is starting."

"Oh that shit? Christ himself could be starting and someone would complain." I didn't play any sports, as tinkering around with my car at Dick's was my extracurricular activity, but had overheard that constantly in down time during classes.

"People were shorter back then so probably." I had a vivid flash of Jesus in a basketball jersey nailed to the cross at center court, waiting for the game to start. Taking another drink, I did my best to leave that image behind and even now, typing it leaves me at a loss. A comedian, I ain't.

The veteran of dozens of these mornings came by and took our orders, Jamie going for the waffles again and me with a full country breakfast. I had a long shift later and homework that was piling up despite my desperate attempts to ignore it, so I obviously needed gravy to propel me through the day.

"So, remember the last time we hung out?" Wasn't sure if the caffeine had kicked in but I was feeling more awake and slightly jittery, as if only now realizing what I was going to ask. And besides, it was distract Jamie from the rest of his worries!

"Kinda hard to forget." Small points of color bloomed in his cheeks as he sipped from the straw, glancing out at the all the older people absorbed in their own conversations and lives before turning back to me, lips still puckered. My heart was hammering, either from seeing Jamie coming alive or what I was going to say and what it might lead to. Fumbling out my phone, I pulled up the picture I'd taken and tried to figure out how to describe this.

"I, uh, After last time I thought this might be something you'd be interested in?" That sounded so fucking stupid that I pushed my phone over to him and busied myself with taking a drink. Now it was my turn to watch him out of the corner of my eyes, him picking up the phone and using a finger and thumb to increase the size of the image.

Jamie's eyes went wide and he looked up at me, then back down as if not believing what he was seeing. He blew the image up further, squinting as if to read what little text there was on the boxes.

"It's what you think it is." I confirmed that for Jamie, only continued to sit there stupefied. Darkening the screen, he slid my phone across the table back towards me and sat there in silence for a bit, opening his mouth a few times and closing it without a sound.

"I guess I'm curious as to why...?" Now it was my turn to think it over, trying to phrase this in a way that made sense to him.

"Ya said it the other night, me behind you felt right. Well, this is just... More." I was leaning forward, not talking loudly but making sure I was heard over the racket of previous generations.

"There's a difference between what we've done and well, that!" He gestured to my phone, color high.

"True but remember: I won't ask you to do something I wouldn't do." There it was, out in the open and all the sudden the condoms and lube laying under my bed now mattered. Jamie opened his mouth, paused, closed it and looked at me with an expression that made me giggle.

"Really?" I nodded and he was cut off by the arrival of our food, the smell making my mouth water and putting the conversation on hold. Freeing my fork from the napkin secured bout it, I began to demolish nearly everything on my plate.

By the time my stomach protested what I was doing to it, Jamie wiped his mouth and spoke.

"Your uh, proposition interests and scares me." Taking a drink, I chuckled at his honesty. "Have you done that before?" This was my life now, discussing anal sex over breakfast.

"Nope. I did get some advice and as long as we take it slow, it should be fine." That was the theory anyway.

"So um..." Picking at the remains of his waffle, Jamie finally spit out the words: "Who goes first?" Now it was my turn to attempt to speak then realize I had nothing. Peering into my Mountain Dew as if it had any answers, I made up my mind.

"I will." Biting his lower lip in a way that would haunt me the rest of the week, Jamie managed a "Are you sure?'

"I've had my way with you so it's only fair you get to do the same. Question now is when do we have time?" Brow furrowing in thought, Jamie pulled out his phone and consulted a schedule, with me following suit. The battle hardened waitress came by and took our plates as I discovered next week was fucked, with Thanksgiving waiting at the end of it.

"Shit." That came from Jamie and I completely understood the annoyance contained in that one word.

"Right?!" I had to go home for Thanksgiving, there was no way around that. "What about the weekend after? Come back a day early and hang out Saturday?" Jamie mulled that over as I talked myself into it. I'd have enough homework piled up and studying to be done for it to be a valid excuse.

"Yeah... Yeah, that should work." There wasn't much enthusiasm in his voice but he nodded, cheeks blazing as we set a date for him to fuck my butt.

"I'll mess around with one of the plugs over the week, to be ready." His face burned brighter, somehow, and he jumped when the waitress dropped off the bill, making me laugh and he went over the edge too. The reason didn't matter, only that we found relief.

We left all the lingering old people behind and paid, getting out of there and back into the cold. Jamie looked to be in a better mood and who could blame him? In under a week he was going to be getting laid for the first time!

"So, after Saturday it will be my turn to uh... My turn, right?" I bit the inside of my cheek to keep from laughing as the total absurdity tried to drag me into madness. Instead, I swallowed all but a single peal of laughter and got my shit back under control. Navigating out of the parking lot, I got us going back towards the college as work waited all too soon.

"Yeah, yep, sorry. Probably not going to have much free time til next year but we'll figure it out." Pulling into a parking spot by his dorm, I leaned over and kissed him, his tongue finding mine, a curl of his hair brushing my nose. I broke away, breathing hard, Jamie's hand on the door handle as he grinned.

"I'm glad Tom talked me into going to that party." I grinned, seeing the shy boy trying to stay in the background anew, knowing what lay under his ill fitting clothing was very different from what he had been wearing the first time we met.

"Me too." With that said, he left with a perk in his step, the hoodie swallowing any hint of breasts. I powered through the rest of my day, making it home after dark and showering before settling down for some homework before I passed out.

All day the thought of what Jamie and I were going to be getting up to invaded my mind and made work a nightmare. At least with me working in the cooler with some earbuds in, I could distract myself and got a good chunk of work done in the process. But now that I was alone, in private, there was nothing to keep me occupied. Homework? Yeah, not a chance.

I pulled the bag out from under my bad, digging out a boxed butt plug and the bottle of lube. Opening the box, I slid the plug out and looked it over. It wasn't very wide except at the flared bottom which kept it from falling in. A quick scan over the back of the box only informed me it was made of silicon and wasn't meant for medical purposes. Good to know?

Heat was welling up where Jamie had yet to venture and was going to continue to be ignored at this rate. I'd never given sticking anything up my butt much thought before yet here I was, holding a thing meant for that purpose and nothing more. Plus the lube to make it happen.

Consulting my computer, I opened a new incognito window and searched 'how to use butt plug'. I knew it wasn't that complicated but I needed to know how to handle this for when it was Jamie's turn. A helpful article was near the top and I read it, finding the attendant from the adult toy store had been absolutely correct with all the info she'd given. Lube, finger first, then two, plug followed and stayed there for a while, then commence with the fucking.

Getting up out of bed, I went to my still organized closet and found a ratty shirt. Laying that down, I thought for a second and fished about for the condoms. Taking one, I tossed it on the bed and figured I had everything I needed for this little experiment. Was probably the closest to science I'd done all year.

Flicking off the main light, I opted for the lamp on my desk, setting the mood. Taking off my pajama pants, I laid on the towel and spread my legs, running a teasing finger down the slip of pink showing through already wet lips. Instead of doing the usual, I grabbed the bottle of lube and cracked it open, smelling cherry as I leaned it against my hips, finding the condom and tearing it open. The rubbery texture was something I'd only felt twice before but this time I'd be the one putting it on.

Unrolling the condom over my middle finger, I lubed it up and reached between my legs to try something new for a boy, something my parents had told me to never do if it made me feel uncomfortable. Yet that hadn't happened, Jamie had asked nothing of me that I didn't already want to do.

Those thoughts stopped as my finger ran over the entrance that would be getting some action in the up coming week. Once I had it's position right, not too easy when I could see, I added more lube. Both the woman at the adult toy store and the article had insisted upon lube, all the lube, death, taxes and lube and so I took the hint and only stopped when I felt it running down my crack.

Slick and ready, I found the back door with my protected finger and pushed, ready to get this under way... And flinched away from my own touch. Letting loose a breath I didn't realize I was holding it, I grabbed my phone with my off hand and clumsily got YouTube open and punched in Fleetwood Mac, scrolling down until I saw Dreams, letting Stevie Nicks' voice soothe me. If this was going to happen, and it was going to so I could have my turn, I needed to slow it down.

Adding a bit more lube, cause why not, I took my time exploring the path less traveled. When the song ended, I set it on loop as I put a bit of pressure on what was under my finger and sucked in air as I felt it give, on both fronts. Another deep breath and I eased in, feeling the latex of the condom where nothing had entered before.

I lay there, triumphant, having lodged a finger up my butt. Truly, the reason why I had come to college and worth going into debt for. Shifting to get more comfortable, I moved too much and felt my finger slipping out. Lodged that back in, I felt around inside of me, finding this sensation different from what I'd done before. Once past that tight entrance it opened up but even one of my fingers felt hugely intrusive. Looking over at the butt plug laying beside me, it now appeared more challenging than I had previously figured. Without that, there was little chance of getting Jamie in me so I carefully removed my finger, added another to the condom and slipped those in.

That time was easier but I still took it slow, the song ending then restarting as I worked them out, then back in, that old familiar dance in a new locale. Resistance fought me but a steady persistence won through. Laying in what had to be one of the most undignified positions possible, I snatched up the plug and prepared to face this.

Lubing the lower half of the toy, I took another deep, steadying breath before removing my fingers and shaking the condom off. Taking hold of the flat base, I dipped it between my legs and felt the cool, slick surface of it poking about. Raising my hips to get a better angle, I got it lined up and closed my eyes, letting Dreams roll over me before I began what had to be done. I uttered a hiss as that cone started widened yet I kept it coming, the chaotic darkness behind my eyelids roiling as I bit back growing discomfort until relief came, along with a fullness that made my back arch.

Wiping my hand on the shirt, I lay there, experiencing this newest, odd feeling. There was most certainly something stuck up my butt yet it wasn't as bad as I figured. Sitting up, I shifted some and found that it didn't impede me much, if at all. Jamie was far bigger than this thing and only now did I comprehend what I'd gotten myself into.

Still, I was happy with what little progress I'd made and settled down to do some homework and instead typed all this out, the plug being in the whole time. It's not easy to forget it being there and I can only hope it does the job when Saturday rolls around.

I don't even know how to process my emotions about Saturday. Excitement? Nervousness? How was Jamie feeling, knowing we're trading off on this?

How the fuck am I going to be able to sleep tonight?! And the rest of the week?